7-Day Cruise from Kos to Santorini aboard the Walkabout 43
Destination: Cyclades, Greece | Duration: 7 days/7 nights | Embarkation: Kos | Disembarkation: Santorini | Islands: Kos, Nisyros, Astypalea, Anafi, Santorini | Formula: Exclusive charter with skipper or Cabin charter | Highlights: Sporty sailing, bay exploration, authentic villages.
Our sailing cruise from the Dodecanese to the heart of the Cyclades reveals an exciting adventure that combines the challenge of longer and more demanding sailing passages with the pleasure of relaxing days dedicated to exploring crystalline bays and deserted islets, far from the routes beaten by mass tourism. Our journey will take us to discover hidden gems such as Anafi, Astypalea and Nisyros and neighboring islets, all islands that preserve their wild and authentic beauty intact.
Our journey begins on the island of Kos, with its mix of history and modernity. Our sailboat awaits you moored in a quiet corner, ready to welcome you and offer you moments of relaxation before beginning our boat journey towards remote and fascinating islands.
Anafi is the first of these pearls, a fascinating and isolated island, perfect for those seeking peace and authenticity. With its unspoiled beaches and the majestic monolith of Kalamos, one of the tallest in the Mediterranean, Anafi offers an experience out of time, far from mass tourism and dominated by nature.
Astypalea, on the other hand, is an island that holds a unique charm thanks to its characteristic butterfly shape and its position straddling the Dodecanese and the Cyclades. With its Venetian castle and the white houses of the village, the island offers spectacular views and a magical atmosphere, perfect for those who love to combine history and unspoiled nature.
Aboard our modern and high-performance boat, every mile sailed becomes a moment of entertainment. Our vessel, designed to combine comfort and performance, allows us to face the sea with confidence, transforming navigation into a pleasant and rewarding experience. The stability and speed of the boat blend perfectly with the skill of your skippers, expert sea navigators who guide the boat through the turquoise waters of the Aegean Sea with experience and passion.
But it’s not just the sailing that makes this cruise unforgettable. The skippers, in addition to being skilled sailors, also prove to be excellent cooks, capable of transforming every meal on board into an opportunity to enjoy exquisite dishes. Using fresh ingredients and gourmet recipes, they delight us with culinary creations that reflect not only the tradition and flavors of Italian cuisine, but also a refined reinterpretation of ethnic cuisine. Our days are thus marked by moments of conviviality and gastronomic pleasure.
The cruise concludes with arrival in spectacular Santorini, surrounded by the beauty of the island and memories of this extraordinary adventure in the heart of the Mediterranean. Santorini offers the opportunity to extend the trip with visits to the most beautiful of the Cyclades, the perfect ending to an unforgettable cruise.
Price and Available Dates: JULY 25, 2026 or check the 2026 cruise schedule.
Included Services Full details: Walkabout Charter Rental Terms
⭐ Rating: 4.9/5 (based on 47 reviews on Google, TripAdvisor and Facebook)
Day-by-Day Itinerary
Saturday – Kos, Kardamena: Embarkation
Embarkation port: Kardamena, Kos (36.7632°N, 27.1331°E) | Embarkation: 6:00 PM | Don’t miss: Kos town, Asklepion, Hippocrates’ plane tree, Knights’ castle | Connections: Kos Airport (KGS) – 8 km from Kardamena (Bus or Taxi)
Embarkation at 6:00 PM, we will be anchored outside the small port of Kardamena. Settling into the cabins of the Walkabout 43, safety briefing, presentation of the itinerary. Then a short sail to reach Giali where we’ll anchor in a deserted bay. Dinner on board.
Sunday – Nisyros, The Volcano Island
Arrival: Nisyros (36° 36.9130′ N, 027° 51.5179′ E) | Distance: 16 nautical miles | Sailing time: 3 hours | Don’t miss: | Activities:
After breakfast, early in the morning to make the most of this day, we hoist the sails for a short sail to the island of Nisyros. We moor in the picturesque small port of Pali, a place that preserves the authentic charm of the Dodecanese islands.
Nisyros is famous for its active volcano, and visiting the caldera is an unforgettable experience. You can walk inside the Stephanos crater, where fumaroles emit steam and sulfur, reminding us of the primordial force of the earth. Not far away, the village of Nikia awaits you with its narrow alleys, white houses and breathtaking views of the caldera.
Another gem of Nisyros is Mandraki, the island’s capital, with its fascinating Monastery of Panagia Spiliani, perched on a hill. Here you can explore the streets decorated with volcanic stone mosaics and savor the unique atmosphere of this small community.
Don’t miss tasting local specialties in one of the traditional tavernas, such as pithia (chickpea meatballs) or kapsali (typical goat cheese of the island), for an authentic immersion in the island’s gastronomic culture.
Dinner at a taverna.
Monday – Astypalea
Arrival: Astypalea (36° 31.9020′ N, 026° 28.2055′ E) | Distance: 35 nautical miles | Sailing time: 5-6 hours
The day begins with an early wake-up. Today the longest sail of the week awaits us, we leave Nisyros behind and point the bow towards Astypalea, taking advantage of the beam wind that will take us straight to this hidden pearl of the Cyclades.
Astypalea welcomes us revealing its unmistakable butterfly shape, unique and fascinating. Located on the border between the Dodecanese and the Cyclades, this jewel island is a perfect blend of culture and breathtaking landscapes. We drop anchor in one of its hidden bays for a relaxing break and a delicious lunch on board. The afternoon is dedicated to relaxation and discovering the crystal-clear waters of Astypalea, perfect for a rejuvenating swim or to lie in the sun, enjoying the unspoiled nature that surrounds us.
As the sun sets, the bay of Astypalea transforms into a magical and timeless place.
Dinner on board.
Tuesday – Astypalea
Arrival: Astypalea (36° 33.8663′ N, 026° 21.4100′ E) | Distance: 8 nautical miles | Sailing time: 1-2 hours
After a hearty breakfast on board, we prepare to explore the enchanting bays of the small islands scattered around Astypalea. These hidden gems are sanctuaries for those seeking peace away from the bustle of mass tourism, a refuge for those who wish to immerse themselves in the most authentic nature.
The day flows in harmony with the relaxed rhythm of the small islands, between refreshing swims in transparent waters and regenerating walks along fine sandy beaches. The serenity of the surrounding environment contributes to complete relaxation, whether you choose to sunbathe or prefer more dynamic activities in the water. For sports enthusiasts, there will be plenty of opportunities to practice snorkeling, enjoying the marine wonders that lie just below the surface.
As the sun begins to decline, leaving behind a day of sun and exploration, we move to a bay below the spectacular Chora of Astypalea.
In the late afternoon, a walk to Chora will allow us to experience once again the magic of the island, among the enchanted alleys and the hospitality of small local tavernas. Dinner at a taverna.
Wednesday – Anafi
Arrival: Anafi (36° 21.0162′ N, 025° 49.3473′ E) | Distance: 35 nautical miles | Sailing time: 5-6 hours
The day begins with an early wake-up and a hearty breakfast. A long but fast and pleasant offshore sail will allow us to reach Anafi, a true hidden pearl of the Cyclades.
Anafi, located off the traditional tourist routes, is a sanctuary of peace and authenticity. Its proximity to bustling Santorini amplifies its discreet charm: this island seems suspended in time, offering an oasis of peace and an authentic taste of island life.
Upon arrival, the magic of Anafi will immediately reveal itself in all its beauty. This island, although little known, enchants with its genuine simplicity and unspoiled beaches.
We anchor in the bay in front of the pristine beach, right at the foot of the majestic monolith of Kalamos. This rocky giant, one of the tallest monoliths in the Mediterranean, rises like a silent guardian, a millenary witness to the island’s history.
For the more athletic seeking a touch of adventure, there’s the possibility of following the path that leads to the top of the monolith, where the Monastery of Panagia Kalamiotissa stands. The climb is a unique experience: with each step, the view expands and offers breathtaking glimpses of the sea and coast. The white monastery, set in the rock, integrates perfectly with the landscape and offers a space of tranquility and reflection. From the top, the view of the horizon and the infinite sea invites moments of contemplation and wonder.
Dinner on board.
Thursday – Anafi, The Beautiful Chora
Arrival: Anafi (36° 20.5179′ N, 025° 46.3922′ E) | Distance: 4 nautical miles | Sailing time: 45 minutes
Today we dedicate ourselves completely to relaxation and exploration of the enchanting island of Anafi.
After spending a relaxing morning in the bay, in the afternoon we move to the small port of Anafi. In the late afternoon we walk the steep and spectacular path leading to Chora (there’s also a taxi for those who don’t feel up to it!). We end the day with a stroll through the narrow and winding alleys of Anafi’s center, where the charm of local life seems to have remained intact. The white houses stand out against the evening sky, framed by the violet sunset and the deep blue of the sea. Our dinner takes place in a characteristic taverna overlooking the port below, a scene that seems straight out of a postcard and that gives us a final, unforgettable taste of the island.
Friday – Akrotiri, Santorini
Arrival: Akrotiri (36° 45.8792′ N, 027° 07.9185′ E) | Distance: 12 nautical miles | Sailing time: 2 hours
Today another exciting sail awaits us!
With sails spread to the wind, the boat picks up speed, cutting through the waves with agility and responding promptly to the helm movements. This day of sailing is an authentic experience, full of challenges and adrenaline, perfect for those who love to test their maritime skills.
Those who wish can try steering the boat with the tiller, which allows a more direct sensation of commanding the vessel.
After the morning at sea, we land in Santorini, in a spectacular bay on the east coast. Swimming and relaxation, and then in the afternoon we move to the bay in front of Akrotiri where the cruise ends.
Sunset walk to nearby Red Beach and dinner at a taverna.
Saturday – Akrotiri, Santorini
Disembarkation port: Akrotiri (36° 20.8065′ N, 025° 23.4442′ E) | Disembarkation: 9:00 AM | Don’t miss: Kos town, Asklepion, Hippocrates’ plane tree, Knights’ castle | Connections: Santorini Airport – 14 km from Akrotiri (25 minutes by taxi)
Last breakfast on board. Disembarkation procedures.
FAQ
Is it suitable for those without sailing experience?
No sailing experience is required, however we recommend having tried sailing at least once. This cruise includes a somewhat longer crossing from the Dodecanese to the Cyclades, which requires participants to feel comfortable in open sea and not to suffer from seasickness.
Once the Cyclades area is reached, the itinerary takes place between nearby islands with numerous protected bays and generally calm waters, perfect for those seeking tranquility and relaxation.
The Walkabout 43 is a stable and comfortable boat, ideal for offshore sailing. Our expert skippers take complete care of managing the boat, ensuring safety in all marine weather conditions. Moreover, they are passionate sailors who love to share their passion by teaching the basics of sailing to those who wish to learn.
If you’re not sure whether this cruise is right for you, contact us: we’ll be happy to recommend the itinerary best suited to your needs and experience.
When does the Meltemi blow?
The Meltemi in the Cyclades is generally sustained. It blows mainly July-August with intensity 4-6 Beaufort, making sailing sporty and fun. June and September typically have lighter winds.
Can the itinerary be modified?
Yes, the itinerary is indicative. Skippers adapt it based on weather, group preferences and opportunities. The only constraint is embarkation and disembarkation in Skiathos on Saturday. You can spend more time on certain islands, discover alternative bays, add unplanned stops.
Check out the complete sailing cruise FAQ or contact us directly.
Why Choose This Vacation
Authentic Islands + Sporty Sailing + Unspoiled Nature
Ideal itinerary both for those approaching sailing and also for experienced sailors seeking authentic Greece. Offshore sailing to experience the thrill of more challenging navigation, protected and crystal-clear waters for shelter at night.
Walkabout 43 and Food & Wine
The Walkabout 43 is the perfect boat for this itinerary: comfortable for life on board, safe even with the Meltemi, fun to sail. Three double cabins, two bathrooms, spacious cockpit with teak swim platform to enjoy the sea.
The Sporades are rich in typical products: thyme and pine honey, PDO extra virgin olive oil, goat cheeses, Skopelos dried plums, almonds, very fresh fish. Our skippers prepare traditional Greek dishes with local ingredients purchased on the islands.
Skippers with deep knowledge of the Sporades, the best hidden bays, authentic tavernas frequented by locals, and the area’s marine weather conditions.
Come Prenotare
- Preventivo Personalizzato : Ricevi entro 24h: preventivo dettagliato, disponibilità confermate, condizioni contrattuali.
- Conferma : Paga l’acconto per bloccare la prenotazione.
- Prenota voli : Walkabout Charter fornisce info per voli, traghetti e transfer.
- Preparazione Viaggio : Ricevi lista equipaggiamento consigliato, comunica esigenze alimentari particolari.
- Imbarco! la tua avventura alle Sporadi inizia!
Lesser-Known Cyclades and Spectacular Santorini. Walkabout Charter Takes You There!